CN102382159A - Preparation method of tilmicosin - Google Patents
Preparation method of tilmicosin Download PDFInfo
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- CN102382159A CN102382159A CN2011104031912A CN201110403191A CN102382159A CN 102382159 A CN102382159 A CN 102382159A CN 2011104031912 A CN2011104031912 A CN 2011104031912A CN 201110403191 A CN201110403191 A CN 201110403191A CN 102382159 A CN102382159 A CN 102382159A
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- tilmicosin
- lupetidine
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Abstract
The invention discloses a preparation method of tilmicosin. The method comprises the following steps of: reacting tylosin phosphate serving as a raw material with 3,5-lupetidine by taking alcohol as a solvent and taking anhydrous formic acid as a catalyst at 65-97 DEG C to obtain 20-dihydro-20-deoxy-(3,5-lupetidine-1-radical)tylosin serving as an intermediate; concentrating the solvent; and adding residues into 0.1N sulfuric acid solution for hydrolyzing to obtain tilmicosin, wherein the mass volume ratio of the tylosin phosphate to the alcohol is 1:(2-10), the mass ratio of the tylosin phosphate to the 3,5-lupetidine to the anhydrous formic acid is 1:(0.11-0.17):(5.6-8), and the mass volume ratio of the tylosin phosphate to the 0.1N sulfuric acid solution is 1:(2-6). The reaction formula is shown in the specifications. By adopting the method, the defects of the prior art can be overcome. The method is easy to control, and has high yield and low production cost.
Description
Technical field
The present invention relates to the preparation method of veterinary drug, is a kind of preparation method of tilmicosin.
Background technology
Tilmicosin is the special-purpose antibiolicss of a kind of livestock and poultry.Be mainly used in the mazoitis of control domestic animal pneumonia, fowl mycoplasmosis and lactation animal etc.At present; The method for preparing tilmicosin is that phosphoric acid salt or the tartrate with tylosin is raw material, hydrolysis under water-soluble acidic conditions; Utilize water-insoluble organic solvent amyl acetate-n, ETHYLE ACETATE or methylene dichloride etc. to transfer the alkali extraction again; The extraction organic layer adds formic acid, and 3, the reaction of 5-lupetidine generates tilmicosin.This preparing method's deficiency is: need be through repeatedly soda acid phase inversion extraction; Make the yield losses of tilmicosin bigger, general yield is between 65%-80%, and sub product is more; And complicated operation; Make production cost more high relatively, the suitability for industrialized production difficulty is bigger, causes the range of application of this medicine limited.
Summary of the invention
The objective of the invention is, a kind of preparation method of tilmicosin is provided, it can solve the deficiency of prior art, provides that a kind of working method is easy to control, yield is high, the method for low production cost.
The present invention is for realizing above-mentioned purpose, and realize through following technical scheme: a kind of preparation method of tilmicosin is a raw material with the Webel Tylan Premix; Alcohol is solvent, under 65-97 ℃, is catalyzer and 3 with the anhydrous formic acid, the reaction of 5-lupetidine; Obtain midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin after reacting completely, concentrated solvent; Resistates adds the hydrolysis of 0.1N sulphuric acid soln and obtains tilmicosin; Webel Tylan Premix is 1:2-10 with the mass volume ratio of alcohol, and Webel Tylan Premix and 3, the mass ratio of 5-lupetidine and anhydrous formic acid are 1:0.11-0.17:5.6-8; The mass volume ratio of Webel Tylan Premix and 0.1N sulphuric acid soln is 1:2-6, and reaction formula is following:
Described alcohol is any of methyl alcohol, ethanol or Virahol.
Preparing method's concrete steps of described a kind of tilmicosin are following:
1. get Webel Tylan Premix 100kg, insert in the reaction kettle, add 600L methyl alcohol, be warming up to the refluxing and stirring dissolving, obtain lysate;
2. get anhydrous formic acid 8kg and add the 50L dissolve with methanol, it is subsequent use to obtain mixing solutions after the dissolving;
3. in step lysate 1., add 3,5-lupetidine 17kg drips step mixing solutions 2. again; Under the methanol eddy temperature, react 4-5 hour to complete; Vacuum concentration methyl alcohol obtains midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object;
4. in midbody 20-dihydro-20-deoxidation-(3; 5-lupetidine-1-yl) adds 0.1N sulphuric acid soln 400L in the tylosin liquid object; Reacted 1 hour down at 50 ℃, and then drip 2N sodium hydroxide 50L, transfer alkali to separate out tilmicosin; After the filtration, vacuum-drying obtains tilmicosin 86.9 kg.
The preparation technology of tilmicosin of the present invention is succinct, adopts Webel Tylan Premix directly with 3, and the reaction of 5-lupetidine generates midbody 20-dihydro-20-deoxidation-(3; 5-lupetidine-1-yl) tylosin, hydrolysis can obtain tilmicosin again, and reaction solvent is changed; Avoided repeatedly the soda acid phase inversion to extract the yield losses that causes; Yield is reached about 87%, and reduced separating out of by product, product purity is reached about 90%.Because entire reaction is in a retort, to accomplish, thoroughly having solved needs a plurality of retort productions in the prior art, be easy to problems such as contaminate environment; And make the production cycle shorten about 50%; Significantly improved production efficiency, and production technique is easy to control, the production security height; Be particularly suitable for suitability for industrialized production, production cost significantly reduces.
Embodiment
The preparation method of a kind of tilmicosin of the present invention is a raw material with the Webel Tylan Premix, and alcohol is solvent; Under 65-97 ℃, be catalyzer and 3 with the anhydrous formic acid, the reaction of 5-lupetidine obtains midbody 20-dihydro-20-deoxidation-(3 after reacting completely; 5-lupetidine-1-yl) tylosin, concentrated solvent, resistates add the hydrolysis of 0.1N sulphuric acid soln and obtain tilmicosin; Webel Tylan Premix is 1:2-10 with the mass volume ratio of alcohol, and Webel Tylan Premix and 3, the mass ratio of 5-lupetidine and anhydrous formic acid are 1:0.11-0.17:5.6-8; The mass volume ratio of Webel Tylan Premix and 0.1N sulphuric acid soln is 1:2-6, and reaction formula is following:
The preparation method of tilmicosin of the present invention can have following various embodiments.
Embodiment 1
Preparing method's concrete steps of tilmicosin according to the invention are following:
1. get Webel Tylan Premix 100kg, insert in the reaction kettle, add 600L methyl alcohol, be warming up to the refluxing and stirring dissolving, obtain lysate;
2. get anhydrous formic acid 8kg and add the 50L dissolve with methanol, it is subsequent use to obtain mixing solutions after the dissolving;
3. in step lysate 1., add 3,5-lupetidine 17kg drips step mixing solutions 2. again; Under the methanol eddy temperature, react 4-5 hour to complete; Vacuum concentration methyl alcohol obtains midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object;
4. in midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object, add 0.1N sulphuric acid soln 400L, reacted 1 hour down at 50 ℃; And then dropping 2N sodium hydroxide 50L; Transfer alkali to separate out tilmicosin, after the filtration, vacuum-drying obtains tilmicosin 86.9 kg; Yield is 86.9%, and HPLC content is 89.9%.
Embodiment 2
Preparing method's concrete steps of tilmicosin according to the invention are:
1. get Webel Tylan Premix 100kg, insert in the reaction kettle, add 200L methyl alcohol, be warming up to the refluxing and stirring dissolving, obtain lysate;
2. get anhydrous formic acid 6.8kg and add the 50L dissolve with methanol, it is subsequent use to obtain mixing solutions after the dissolving;
3. in step lysate 1., add 3; 5-lupetidine 14kg; Drip step mixing solutions 2. again, under the methanol eddy temperature, react 5-5.5 hour to complete, vacuum concentration methyl alcohol; Obtain midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object;
4. in midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object, add 0.1N sulphuric acid soln 400L, reacted 1 hour down at 50 ℃; And then dropping 2N sodium hydroxide 50L; Transfer alkali to separate out tilmicosin, after the filtration, vacuum-drying obtains tilmicosin 86.2 kg; Yield is 86.2%, and HPLC content is 89.3%.
Embodiment 3
Preparing method's concrete steps of tilmicosin according to the invention are:
1. get Webel Tylan Premix 100kg, insert in the reaction kettle, add 500L ethanol, be warming up to the refluxing and stirring dissolving, obtain lysate;
2. get anhydrous formic acid 6.8kg and add the 50L dissolve with ethanol, it is subsequent use to obtain mixing solutions after the dissolving;
3. in step lysate 1., add 3; 5-lupetidine 14kg; Drip step mixing solutions 2. again, under the methanol eddy temperature, react 4-4.3 hour to complete, vacuum concentration ethanol; Obtain midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object;
4. in midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object, add 0.1N sulphuric acid soln 400L, reacted 1 hour down at 50 ℃; And then dropping 2N sodium hydroxide 50L; Transfer alkali to separate out tilmicosin, after the filtration, vacuum-drying obtains tilmicosin 84.3 kg; Yield is 86.3%, and HPLC content is 89.7%.
Embodiment 4
Preparing method's concrete steps of tilmicosin according to the invention are:
1. get Webel Tylan Premix 100kg, insert in the reaction kettle, add the 1000L Virahol, be warming up to the refluxing and stirring dissolving, obtain lysate;
2. get anhydrous formic acid 6.8kg and add the dissolving of 50L Virahol, it is subsequent use to obtain mixing solutions after the dissolving;
3. in step lysate 1., add 3; 5-lupetidine 14kg; Drip step mixing solutions 2. again, under the methanol eddy temperature, react 4-4.5 hour to complete, the vacuum concentration Virahol; Obtain midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object;
4. in midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object, add 0.1N sulphuric acid soln 400L, reacted 1 hour down at 50 ℃; And then dropping 2N sodium hydroxide 50L; Transfer alkali to separate out tilmicosin, after the filtration, vacuum-drying obtains tilmicosin 84.1 kg; Yield is 87%, and HPLC content is 90%.
Embodiment 5
Preparing method's concrete steps of tilmicosin according to the invention are:
1. get Webel Tylan Premix 100kg, insert in the reaction kettle, add 700L methyl alcohol, be warming up to the refluxing and stirring dissolving, obtain lysate;
2. get anhydrous formic acid 5.6kg and add the 50L dissolve with methanol, it is subsequent use to obtain mixing solutions after the dissolving;
3. in step lysate 1., add 3; 5-lupetidine 11kg; Drip step mixing solutions 2. again, under the methanol eddy temperature, react 4-4.5 hour to complete, vacuum concentration methyl alcohol; Obtain midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object;
4. in midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object, add 0.1N sulphuric acid soln 400L, reacted 1 hour down at 50 ℃; And then dropping 2N sodium hydroxide 50L; Transfer alkali to separate out tilmicosin, after the filtration, vacuum-drying obtains tilmicosin 81.2 kg; Yield is 86.8%, and HPLC content is 90%.
Embodiment 6
Preparing method's concrete steps of tilmicosin according to the invention are:
1. get Webel Tylan Premix 100kg, insert in the reaction kettle, add 900L methyl alcohol, be warming up to the refluxing and stirring dissolving, obtain lysate;
2. get anhydrous formic acid 5.6kg and add the 50L dissolve with methanol, it is subsequent use to obtain mixing solutions after the dissolving;
3. in step lysate 1., add 3; 5-lupetidine 14kg; Drip step mixing solutions 2. again, under the methanol eddy temperature, react 5.2-5.3 hour to complete, vacuum concentration methyl alcohol; Obtain midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object;
4. in midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object, add 0.1N sulphuric acid soln 200L, reacted 1 hour down at 50 ℃; And then dropping 2N sodium hydroxide 50L; Transfer alkali to separate out tilmicosin, after the filtration, vacuum-drying obtains tilmicosin 85.5 kg; Yield is 86.9%, and HPLC content is 89.7%.
Embodiment 7
Preparing method's concrete steps of tilmicosin of the present invention are:
1. get Webel Tylan Premix 100kg, insert in the reaction kettle, add the 600L Virahol, be warming up to the refluxing and stirring dissolving, obtain lysate;
2. get anhydrous formic acid 5.6kg and add the dissolving of 50L Virahol, it is subsequent use to obtain mixing solutions after the dissolving;
3. in step lysate 1., add 3; 5-lupetidine 14kg; Drip step mixing solutions 2. again, under the methanol eddy temperature, react 4-4.8 hour to complete, the vacuum concentration Virahol; Obtain midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object;
4. in midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object, add 0.1N sulphuric acid soln 600L, reacted 1 hour down at 50 ℃; And then dropping 2N sodium hydroxide 50L; Transfer alkali to separate out tilmicosin, after the filtration, vacuum-drying obtains tilmicosin 85.1kg; Yield is 87%, and HPLC content is 90.2%.
Claims (3)
1. the preparation method of a tilmicosin, it is characterized in that: be raw material with the Webel Tylan Premix, alcohol is solvent; Under 65-97 ℃, be catalyzer and 3 with the anhydrous formic acid, the reaction of 5-lupetidine obtains midbody 20-dihydro-20-deoxidation-(3 after reacting completely; 5-lupetidine-1-yl) tylosin, concentrated solvent, resistates add the hydrolysis of 0.1N sulphuric acid soln and obtain tilmicosin; Webel Tylan Premix is 1:2-10 with the mass volume ratio of alcohol, and Webel Tylan Premix and 3, the mass ratio of 5-lupetidine and anhydrous formic acid are 1:0.11-0.17:5.6-8; The mass volume ratio of Webel Tylan Premix and 0.1N sulphuric acid soln is 1:2-6, and reaction formula is following:
。
2. the preparation method of a kind of tilmicosin according to claim 1, it is characterized in that: described alcohol is any of methyl alcohol, ethanol or Virahol.
3. the preparation method of a kind of tilmicosin according to claim 1, it is characterized in that: concrete steps are following:
1. get Webel Tylan Premix 100kg, insert in the reaction kettle, add 600L methyl alcohol, be warming up to the refluxing and stirring dissolving, obtain lysate;
2. get anhydrous formic acid 8kg and add the 50L dissolve with methanol, it is subsequent use to obtain mixing solutions after the dissolving;
3. in step lysate 1., add 3,5-lupetidine 17kg drips step mixing solutions 2. again; Under the methanol eddy temperature, react 4-5 hour to complete; Vacuum concentration methyl alcohol obtains midbody 20-dihydro-20-deoxidation-(3,5-lupetidine-1-yl) tylosin liquid object;
4. in midbody 20-dihydro-20-deoxidation-(3; 5-lupetidine-1-yl) adds 0.1N sulphuric acid soln 400L in the tylosin liquid object; Reacted 1 hour down at 50 ℃, and then drip 2N sodium hydroxide 50L, transfer alkali to separate out tilmicosin; After the filtration, vacuum-drying obtains tilmicosin 86.9 kg.
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102659878A (en) * | 2012-04-11 | 2012-09-12 | 宁夏泰瑞制药股份有限公司 | Method for synthesizing tilmicosin and tilmicosin phosphate through using tylosin broth |
| CN102746354A (en) * | 2012-07-17 | 2012-10-24 | 宁夏泰瑞制药股份有限公司 | Method for extracting tylosin by tylosin fermentation broth |
| CN103288904A (en) * | 2013-06-28 | 2013-09-11 | 宁夏泰瑞制药股份有限公司 | Preparation method of tilmicosin phosphate crystal |
| CN103483406A (en) * | 2013-09-25 | 2014-01-01 | 宁夏泰瑞制药股份有限公司 | Preparation method for tilmicosin phosphate |
| CN103880903A (en) * | 2014-03-21 | 2014-06-25 | 烟台万润药业有限公司 | Method for preparing tylosin macrolide and derivatives thereof |
| CN104725451A (en) * | 2013-12-18 | 2015-06-24 | 菏泽市方明制药有限公司 | Preparation method of tilmicosin phosphate |
| CN105777828A (en) * | 2014-12-22 | 2016-07-20 | 菏泽市方明制药有限公司 | Method for preparing high-quality tilmicosin through low-quality tylosin |
| CN106749458A (en) * | 2017-02-21 | 2017-05-31 | 西南大学 | The preparation method of malic acid Tilmicosin double salt |
| CN106905397A (en) * | 2017-04-26 | 2017-06-30 | 齐鲁晟华制药有限公司 | A kind of method for preparing Tilmicosin as raw material with tylosin D |
| CN111269275A (en) * | 2020-03-09 | 2020-06-12 | 浙江康牧药业有限公司 | Preparation method of tilmicosin |
| CN115925772A (en) * | 2022-12-20 | 2023-04-07 | 山东久隆恒信药业有限公司 | Synthesis method of tilmicosin |
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Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102659878B (en) * | 2012-04-11 | 2013-12-04 | 宁夏泰瑞制药股份有限公司 | Method for synthesizing tilmicosin and tilmicosin phosphate through using tylosin broth |
| CN102659878A (en) * | 2012-04-11 | 2012-09-12 | 宁夏泰瑞制药股份有限公司 | Method for synthesizing tilmicosin and tilmicosin phosphate through using tylosin broth |
| CN102746354B (en) * | 2012-07-17 | 2014-09-10 | 宁夏泰瑞制药股份有限公司 | Method for extracting tylosin by tylosin fermentation broth |
| CN102746354A (en) * | 2012-07-17 | 2012-10-24 | 宁夏泰瑞制药股份有限公司 | Method for extracting tylosin by tylosin fermentation broth |
| CN103288904A (en) * | 2013-06-28 | 2013-09-11 | 宁夏泰瑞制药股份有限公司 | Preparation method of tilmicosin phosphate crystal |
| CN103288904B (en) * | 2013-06-28 | 2015-07-15 | 宁夏泰瑞制药股份有限公司 | Preparation method of tilmicosin phosphate crystal |
| CN103483406A (en) * | 2013-09-25 | 2014-01-01 | 宁夏泰瑞制药股份有限公司 | Preparation method for tilmicosin phosphate |
| CN104725451A (en) * | 2013-12-18 | 2015-06-24 | 菏泽市方明制药有限公司 | Preparation method of tilmicosin phosphate |
| CN103880903A (en) * | 2014-03-21 | 2014-06-25 | 烟台万润药业有限公司 | Method for preparing tylosin macrolide and derivatives thereof |
| CN103880903B (en) * | 2014-03-21 | 2016-06-15 | 烟台万润药业有限公司 | A kind of preparation method of tylosin class macrolide and derivant thereof |
| CN105777828A (en) * | 2014-12-22 | 2016-07-20 | 菏泽市方明制药有限公司 | Method for preparing high-quality tilmicosin through low-quality tylosin |
| CN106749458A (en) * | 2017-02-21 | 2017-05-31 | 西南大学 | The preparation method of malic acid Tilmicosin double salt |
| CN106905397A (en) * | 2017-04-26 | 2017-06-30 | 齐鲁晟华制药有限公司 | A kind of method for preparing Tilmicosin as raw material with tylosin D |
| CN106905397B (en) * | 2017-04-26 | 2019-11-15 | 齐鲁晟华制药有限公司 | A method of Tilmicosin is prepared using tylosin D as raw material |
| CN111269275A (en) * | 2020-03-09 | 2020-06-12 | 浙江康牧药业有限公司 | Preparation method of tilmicosin |
| CN115925772A (en) * | 2022-12-20 | 2023-04-07 | 山东久隆恒信药业有限公司 | Synthesis method of tilmicosin |
| CN115925772B (en) * | 2022-12-20 | 2023-07-25 | 山东久隆恒信药业有限公司 | Synthesis method of tilmicosin |
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